The “non-nucleophilic” anion [Tf2N]− competes with the nucleophilic Br−: an unexpected trapping in the dediazoniation reaction in ionic liquids

Riccardo Bini; Cinzia Chiappe; Elisa Marmugi; Daniela Pieraccini

doi:10.1039/B514988F

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The “non-nucleophilic” anion [Tf₂N]⁻ competes with the nucleophilic Br⁻: an unexpected trapping in the dediazoniation reaction in ionic liquids†

Riccardo Bini,^a Cinzia Chiappe,*^a Elisa Marmugi^a and Daniela Pieraccini^a

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* Corresponding authors

^a Dipartimento di Chimica Bioorganica e Biofarmacia, via Bonanno 33, Pisa, Italy
E-mail: cinziac@farm.unipi.it
Fax: 39050 2219660
Tel: 39050 2219669

Abstract

Imidazolium ionic liquids containing [Tf₂N]⁻ anion are not as innocent as they are often considered; [Tf₂N]⁻ is more reactive than Br⁻ in heterolytic dediazoniation reactions.

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Supplementary files

ESI-MS spectra of pure [bmim][Br], [bmim][BF ₄], [bmim][Tf ₂N], [emim][I], [emim][Tf ₂N] and of the 1 : 1 mixture [emim][I]–[emim][Br] PDF (165K)

Article information

DOI: https://doi.org/10.1039/B514988F
Article type: Communication
Submitted: 21 Oct 2005
Accepted: 16 Dec 2005
First published: 19 Jan 2006

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Chem. Commun., 2006, 897-899

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The “non-nucleophilic” anion [Tf₂N]⁻ competes with the nucleophilic Br⁻: an unexpected trapping in the dediazoniation reaction in ionic liquids

R. Bini, C. Chiappe, E. Marmugi and D. Pieraccini, Chem. Commun., 2006, 897 DOI: 10.1039/B514988F

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